(1S,2S,3R,4R)-1-(4-methoxybenzylamino)-1-[4-methoxyphenyl]-2,3-O-isopropylidenepentan-2,3-diol | 1301240-40-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2S,3R,4R)-1-(4-methoxybenzylamino)-1-[4-methoxyphenyl]-2,3-O-isopropylidenepentan-2,3-diol
• 英文别名: (1R)-1-[(4R,5S)-5-[(S)-(4-methoxyphenyl)-[(4-methoxyphenyl)methylamino]methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol
• CAS: 1301240-40-3
• 化学式: C₂₃H₃₁NO₅
• 分子量: 401.503
• InChiKey: JMJSODMGLDAPRG-OUWXYEHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  69.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,2S,3R,4R)-1-(4-methoxybenzylamino)-1-[4-methoxyphenyl]-2,3-O-isopropylidenepentan-2,3-diol 在 吡啶 、 palladium on carbon 、 氢气 、 甲基磺酰氯 作用下， 以 甲醇 为溶剂， 反应 64.0h， 生成 (3aS,4S,6S,6aR)-4-(4-methoxyphenyl)-2,2,6-trimethyl-4,5,6,6a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole
  参考文献：
  名称：

  Synthesis and Fucosidase Inhibitory Study of Unnatural Pyrrolidine Alkaloid 4-epi-(+)-Codonopsinine

  摘要：

  The total synthesis of enantiopure 4-epi-(+)-codonopsinine was achieved in 10 steps starting from D-ribose as a chiral building block. The key step involved a highly stereoselective nucleophilic addition of a Grignard reagent to a protected ribosylamine. Synthesis of the N-desmethyl derivative and its p-tolyl analogue was also accomplished, and the compounds were assayed against alpha-fucosidase.

  DOI：

  10.1021/jo200176u
• 作为产物：
  描述：

  5-deoxy-2,3-O-isopropylidene-D-ribofuranose 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 31.0h， 生成 (1S,2S,3R,4R)-1-(4-methoxybenzylamino)-1-[4-methoxyphenyl]-2,3-O-isopropylidenepentan-2,3-diol
  参考文献：
  名称：

  Synthesis and Fucosidase Inhibitory Study of Unnatural Pyrrolidine Alkaloid 4-epi-(+)-Codonopsinine

  摘要：

  The total synthesis of enantiopure 4-epi-(+)-codonopsinine was achieved in 10 steps starting from D-ribose as a chiral building block. The key step involved a highly stereoselective nucleophilic addition of a Grignard reagent to a protected ribosylamine. Synthesis of the N-desmethyl derivative and its p-tolyl analogue was also accomplished, and the compounds were assayed against alpha-fucosidase.

  DOI：

  10.1021/jo200176u

文献信息

• Synthesis and Fucosidase Inhibitory Study of Unnatural Pyrrolidine Alkaloid 4-<i>epi</i>-(+)-Codonopsinine
  作者：Alexis Kotland、Fabien Accadbled、Koen Robeyns、Jean-Bernard Behr

  DOI：10.1021/jo200176u

  日期：2011.5.20

  The total synthesis of enantiopure 4-epi-(+)-codonopsinine was achieved in 10 steps starting from D-ribose as a chiral building block. The key step involved a highly stereoselective nucleophilic addition of a Grignard reagent to a protected ribosylamine. Synthesis of the N-desmethyl derivative and its p-tolyl analogue was also accomplished, and the compounds were assayed against alpha-fucosidase.